Bridgeport, CT Cross Country Skiing Trails and Maps

987 Reviews

Looking for the best Cross Country Skiing trails around Bridgeport?

Find the top rated cross country skiing trails in Bridgeport, whether you're looking for an easy short cross country skiing trail or a long cross country skiing trail, you'll find what you're looking for. Click on a cross country skiing trail below to find trail descriptions, trail maps, photos, and reviews.

A part of Connecticut's first bus rapid transit line, the CTfastrak Trail serves as recreational and multi-use path for walking and bicycling between Downtown New Britain and Newington Junction. The...

Running alongside both the Housatonic and Naugatuck Rivers, the Derby Greenway demonstrates a seamless integration of Connecticut’s natural river systems and parks with man-made interventions of the...

A dozen miles west of Connecticut’s capital of Hartford, the Farmington River Trail forms a 16.5-mile arc that connects to the larger Farmington Canal Heritage Trail on both ends. The rail-trail was...

The 3.1-mile Kress Family Trail in Roxbury occupies the former route of the Shepaug Valley Railroad (the Shepaug, Litchfield and Northern Railroad). The railroad was famously known as the “crookedest...

The first phase of the New Milford River Trail runs southeast from Gaylordsville via the scenic but lightly traveled River Road, through Sega Meadows to Boardman Bridge, a distance of about 5 miles....

When completed, the Norwalk River Valley Trail will run from Danbury to Long Island Sound in southwestern Connecticut, for a total of about 27 miles. Currently, several disconnected sections totaling...

The Old Croton Aqueduct State Historic Park follows the route of the Old Croton Aqueduct, which carried water to New York City from 1842 to 1955. Most of the structure lies beneath the trail and has...

Fahnestock State Park is a relatively undiscovered gems in the New York State Park System. Located a few miles east of Cold Spring Village on Rt. 301 (Main Street), the park jurisdiction was recently...

The Quarry Trail is currently a 600-foot long unimproved strip of land along what is known as Quarry Road in the Village of Hastings-on-Hudson, NY. The trail links Old Croton Aqueduct State Historic...

The Ridgefield Rail-Trail meanders for nearly 2.5 miles through the forested exburbs of Ridgefield, Connecticut. The trail passes among suburban acreages, along a creek at one point, and past a couple...

When complete, Connecticut’s Shoreline Greenway Trail will be a scenic 25-mile route through four quaint New England towns off Long Island Sound. From Lighthouse Point to Hammonasset Beach State Park,...

The first phase of the New Milford River Trail runs southeast from Gaylordsville via the scenic but lightly traveled River Road, through Sega Meadows to Boardman Bridge, a distance of about 5 miles....

A part of Connecticut's first bus rapid transit line, the CTfastrak Trail serves as recreational and multi-use path for walking and bicycling between Downtown New Britain and Newington Junction. The...

A dozen miles west of Connecticut’s capital of Hartford, the Farmington River Trail forms a 16.5-mile arc that connects to the larger Farmington Canal Heritage Trail on both ends. The rail-trail was...

When complete, Connecticut’s Shoreline Greenway Trail will be a scenic 25-mile route through four quaint New England towns off Long Island Sound. From Lighthouse Point to Hammonasset Beach State Park,...

The 3.1-mile Kress Family Trail in Roxbury occupies the former route of the Shepaug Valley Railroad (the Shepaug, Litchfield and Northern Railroad). The railroad was famously known as the “crookedest...

When completed, the Norwalk River Valley Trail will run from Danbury to Long Island Sound in southwestern Connecticut, for a total of about 27 miles. Currently, several disconnected sections totaling...

Running alongside both the Housatonic and Naugatuck Rivers, the Derby Greenway demonstrates a seamless integration of Connecticut’s natural river systems and parks with man-made interventions of the...

When complete, Connecticut’s Shoreline Greenway Trail will be a scenic 25-mile route through four quaint New England towns off Long Island Sound. From Lighthouse Point to Hammonasset Beach State Park,...

The first phase of the New Milford River Trail runs southeast from Gaylordsville via the scenic but lightly traveled River Road, through Sega Meadows to Boardman Bridge, a distance of about 5 miles....

The Old Croton Aqueduct State Historic Park follows the route of the Old Croton Aqueduct, which carried water to New York City from 1842 to 1955. Most of the structure lies beneath the trail and has...

Fahnestock State Park is a relatively undiscovered gems in the New York State Park System. Located a few miles east of Cold Spring Village on Rt. 301 (Main Street), the park jurisdiction was recently...

The Ridgefield Rail-Trail meanders for nearly 2.5 miles through the forested exburbs of Ridgefield, Connecticut. The trail passes among suburban acreages, along a creek at one point, and past a couple...

A dozen miles west of Connecticut’s capital of Hartford, the Farmington River Trail forms a 16.5-mile arc that connects to the larger Farmington Canal Heritage Trail on both ends. The rail-trail was...

The 3.1-mile Kress Family Trail in Roxbury occupies the former route of the Shepaug Valley Railroad (the Shepaug, Litchfield and Northern Railroad). The railroad was famously known as the “crookedest...

When completed, the Norwalk River Valley Trail will run from Danbury to Long Island Sound in southwestern Connecticut, for a total of about 27 miles. Currently, several disconnected sections totaling...

The Quarry Trail is currently a 600-foot long unimproved strip of land along what is known as Quarry Road in the Village of Hastings-on-Hudson, NY. The trail links Old Croton Aqueduct State Historic...

A dozen miles west of Connecticut’s capital of Hartford, the Farmington River Trail forms a 16.5-mile arc that connects to the larger Farmington Canal Heritage Trail on both ends. The rail-trail was...

Running alongside both the Housatonic and Naugatuck Rivers, the Derby Greenway demonstrates a seamless integration of Connecticut’s natural river systems and parks with man-made interventions of the...

Fahnestock State Park is a relatively undiscovered gems in the New York State Park System. Located a few miles east of Cold Spring Village on Rt. 301 (Main Street), the park jurisdiction was recently...

Recent Trail Reviews

Hudson River Greenway

great trail with incredible sights

Cross Island Parkway Trail

Newly paved trail is now open from the marina to Northern Blvd. This is a great ride especially during the week when it is not so crowded. As another reviewer stated one can extend their ride into nearby Fort Totten.

Newly paved trail is now open from the marina to Northern Blvd. This is a great ride especially during the week when it is not so crowded. As another reviewer stated one can extend their ride into nearby Fort Totten.

Pequonnock River Trail

Dangerous crossing- Whitney Ave, Trumbull

I love to walk the trail and have since 1971, the cross over on Whitney Ave in Trumbull is Terrifying, The cars cannot see any one passing the road way until they are in the roadway. The line of sight is completely obscured by vegetation and the small sign in the middle of the Street??? I have seen people run right across the road with out even slowing down prior to or while crossing Whitney Ave. I personally saw a woman hit the side of a car as she could not stop running in time to avoid the car. This section is an accident waiting to happen. Whitney Ave. crossing needs to be safer for both motorist and trail user.

Bronx River Greenway

Short version starting in Bronxville to Kensico Dam (24mi RT)

No meter parking along Kimball Ave before Palmer Rd.
To avoid getting lost trying to connect to the bike path after passing the Scarsdales Train Station: exit at the station go north on East Pkwy; Rt on Crane Rd; Lf on Fox Meadows Rd (after Fenimore Rd) it changes to Walworth Ave and Lf on Greenacres Ave. The 2nd entrance to the trail is about 1/5 mile on the right.
There are restrooms when you reach the Kensico Dam.

EPCAL Alternative Transportation Path

Great Path - Good for Beginners and Families

Paved path of just about 8.5 miles (all off the regular roadways) provides a great pathway for all skill levels.
Beginners can take a leisurely ride with gradual inclines or more experienced riders can challenge themselves with speed and cadence. The path is completely free of roadway dangers as it is only open to walkers, bikers, skaters, etc.
It has quite a bit of shady areas to stay out of direct sun due to its location near the woods.
Some nice natural scenery. Start/end point located near Veteran Memorial and Isaac Dog Park for other points of interest.

Shore Parkway Greenway Trail

Great path for any sport or hobby

This bike path needs to be Swept with a sanitation truck. Sweeper at least once a month I have gotten so many bike tire flats I usually ride from howard beach to the verrazano and back or I do the 20 mile loop to Rockaway and back home it needs a good cleaning and May be more lighting Thank YOU

Air Line State Park Trail

Response to Construction News

In April 2018 the Windham Town Council approved $1,300,000 for rehabilitation on the Willimantic River bridge behind Mackeys. This would include 800 feet of trail. It was put out for bids due on July 26th. I haven't seen any work yet. There is still the bridge over the Hop River which looks to be in terrible shape and may never be repaired.

Farmington Canal Heritage Trail

Last gap in Cheshire closed

Quick update that a stretch of trail less than one mile between Cornwall Av. and West Main St. in Cheshire is now officially opened, avoiding a detour onto Willow St. There is now a continuous, paved, off-road stretch of trail some 25 miles from Temple St. in downtown New Haven to Lazy Lane in Southington.

Air Line State Park Trail

Construction News

I just road the Airline Trail across the Willimantic River and then toward the newer ending at Mackie's Ag. Store near the Columbia town line. It was in fine shape. However, what I was looking for is evidence that the work on the Willimantic River bridge was started. I found nothing underway. I road to the easterly end of the Hop River Trail hoping that it was starting at that end. No such luck. Does anyone out there have any information on when this section will be started?

Charter Oak Greenway

Construction News

As of September 8th 2018 there is only one thing holding back the expansion of the Charter Oak Trail from Porter Street to the Hop River Trail in Bolton, the bridge over Camp Meeting Road. It should be the completion of just a few details that will allow this section to be open to the public: accepting the last bridges and some land scaping work. Once the bureaucracy is done, riders will be able to connect from East Hartford to Bolton and beyond. That's about 15 miles of the Charter Oak Trail and 20 miles of the Hop River Trail that will be connected, finally. Of note, there are two more bridges in Windham and Columbia at the eastern end of the Hop River Trail that are going to bid this fall. Once done, it will open a trail from the Hartford area to Pomfret CT. Be patient. What's another year or so to get all these trails linked.

Farmington Canal Heritage Trail

Love the trails

I am lucky emough to live 1/2 mi from the Farmington Valley Trail and use it quite frequently along with a few of my friends.
I used to ride my horse along this route before it was scheduled for paving for a rail trail. Back then very FEW people used it. Mostly young motorcross kids and horseback riders.
Since it has been paved - horses are now NOT ALLOWED!! (Too bad for us); but as I have moved away from horse riding to personal trail use I am SO HAPPY that I have this wonderful gift in my back yard. There are many many miles and it spans on into southern massachusetts as well.
The trail itself is wonderful; paved, stripe’d and mowed in my area. I have ridden into Mass and south to Simsbury. Before my section was paved I had to load my bike and drive to Simsbury and unload, reload etc. Now, I just hope onto bike (or walk) and go for as long or far as I choose. The scenery is mostly rural, treed and very few homes are seen unless you are crossing streets. I know there are black bears near our home (area) but have not SEEN one ON the trail (daytime use).
It is SUCH a marvelous thing - and I see dozens and dozens of folks biking, walking, & rollerblading. Its a joy to be out in nature!!

Pequonnock River Trail

Definitely start at Pepper. Creepy at Swamp.

Labor Day weekend, 2018
I had a hard time finding the entrance at Swamp Road, it is only marked “No authorized vehicles” and, more ominously, “Police are monitoring illegal activities.” My 7-yr-old son was alarmed and frightened by the signs and the broken down structures, rusty dumped machines and the lack of a path about 500 feet in. Instead it’s a broad overgrown cement yard - too broad to find the narrow throughway to continue south. We rode around a bit on the broken glass and shards, and left feeling unsafe.
I will probably return without him to try again, as I would really like to find a path off the street to get to Trumbull, but I can’t recommend this segment above Pepper.